Dimethylformamide → HCID 70982118, compound

HRID 1409331Notes

Reaction equation

HRID 1409331 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]2[CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=[C:2]12.[NH2:12][C@@H:13]([CH3:30])[CH2:14][N:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:27]=[C:26]([F:28])[C:23]([C:24]#[N:25])=[C:22]([Cl:29])[CH:21]=2)=[N:16]1.CN(C=O)C>O.C(OCC)(=O)C>[Cl:29][C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][N:15]([CH2:14][C@@H:13]([NH:12][C:9]([C:7]3[N:8]=[C:2]4[N:3]([CH:6]=3)[CH:4]=[CH:5][S:1]4)=[O:11])[CH3:30])[N:16]=2)[CH:27]=[C:26]([F:28])[C:23]=1[C:24]#[N:25]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 2759354Imidazo[2,1-b]thiazole-6-carboxylic acidHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 70982118HCID 70982118, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from imidazo[2,1-b]thiazole-6-carboxylic acid (1.041 mmol, 0.175 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (1.041 mmol, 0.290 g). DMF (10 ml) was used as the solvent and the reaction time was 2 days. The work up was done by diluting the reaction mixture with water and ethyl acetate and washing it with 2M Na2CO3, water and brine. The combined organics were dried, filtered and eveaporated. The crude product was purified by flash chromatography. 0.186 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 1.24 (d, 3H), 4.32-4.39 (m, 1H), 4.40-4.47 (m, 1H), 4.53-4.61 (m, 1H), 6.79 (d, 1H), 7.20 (d, 1H), 7.73 (d, 1H), 7.76 (d, 1H), 7.77-7.81 (m, 1H), 7.89-7.91 (m, 1H), 8.10 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. washwashing it with 2M Na2CO3, water and brine
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-533064f977b54f919dfe695689532f6d
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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